The Match: Tiger Woods vs. Phil Mickelson

Who will win the hyped match between Phil Mickelson and Tiger Woods on Friday? We asked 40 caddies and the majority think it will be a landslide.

Welcome to this special edition of “The Caddie Line: The Match!”

All eyes (maybe) will be on Shadow Creek in Las Vegas this Friday afternoon, as Tiger Woods squares off against Phil Mickelson in a winner-take-all, $9 million match that promises loads of side bets that will up the total of money in play.

Intriguing? Eh. Many scowled at the $19.99 pay-per-view price tag.

But fun? Most definitely. It’s a match between two of the most influential and recognizable golfers of all time.

And, let’s face it, $9 million isn’t going to do anything to change their respectful lifestyles (gasp!). But you can bet that neither wants to lose just because of the bragging rights.

We reached out to 40 PGA Tour caddies – guys that have seen Tiger and Phil play up close for years – to get their take on how “The Match” will play out. They gave their explanations on the condition of anonymity. We’re not trying to get anyone in trouble here. Did you see how long Tiger held a grudge on Paul Tesori over a playful “Tiger Who?” hat at the 2000 Presidents Cup?! (Luckily, they’re longtime buddies now):

By a 26-14 count, the caddies believe Tiger will come out on top.

Here’s their reasoning…

Explanations by caddies who think Tiger will win:

“Eighty wins, 14 majors. Enough said.”

“I made my pick by simple math… every tournament Tiger and Phil are in the same field, Tiger has beat Phil 72 percent of the time. It’s simple. Tiger has and will continue to beat Phil.”

“The G.O.A.T. owns the wannabe G.O.A.T.”

“I like Tiger better and want him to win.”

“Tiger is the G.O.A.T.”

“He’s the G.O.A.T.”

“Obviously neither one of them cares about the money. And while I think Phil cares about winning this more than Tiger does, I think Tiger will win solely because he doesn’t want Phil to be able to talk trash to him going forward. It’s like playing basketball in the driveway with your little brother. You don’t get much satisfaction out of beating him, but you can’t let him win because he’ll never stop talking about it.”

“Both struggling but Phil eats more doughnuts.”

“I watched the way they each played at the end of the season. Phil couldn’t find the planet. TW will wear him down.”

“I think Tiger has nicer eyes and he will hypnotize big Phil into hitting a few bad shots.”

“Because Phil has been playing like shite.”

“Tiger is back in form and Phil’s hair has gotten a bit out of control… it’s causing him to hang back a bit too much. If he stays away from the long-sleeve button down, he can keep it closer.”

“Tiger is the G.O.A.T.!”

“Tiger has owned Phil. He will continue to own Phil.”

“Two words: Momentum and confidence. Tiger is starting to feel like his dominating self with the shots he’s able to execute now that he is healthy.”

“Phil is not playing near good enough to compete with a healthy Tiger… it will not even be close. I would not pay to watch this match!”

“The G.O.A.T. strikes back.”

“Tiger doesn’t want to lose this. He wants to bury Phil.”

“Tiger wins the match but… Phil is a better gambler. He will win all the side bets.”

“He’s a better player, knows the course and will put the ball in play off the tee more often.”

“Tiger has the ability to mentally win the big match! He seems to always find the will to never let go even if he is down! Phil will be a great opponent, but I feel Tiger wins.”

“Obviously neither one of them cares about the money. And while I think Phil cares about winning this more than Tiger does, I think Tiger will win solely because he doesn’t want Phil to be able to talk trash to him going forward. It’s like playing basketball in the driveway with your little brother. You don’t get much satisfaction out of beating him, but you can’t let him win because he’ll never stop talking about it.”

“He’s the modern era G.O.A.T.”

“Tiger is playing great and doesn’t want Phil to win against him.”

“It’s a guess. I’ll be honest… I have zero interest in this event. I can’t understand the hype.”

“Tiger is in his head.”

Explanations by caddies who think Phil will win:

“He cares more. Tiger don’t give two shits!”

“I think there’ll be more gamesmanship by Phil and he’s definitely seemed like the one who’s more into this whole charade from the start. Could be entertaining but my expectations are low.”

“Phil wants it more. This kind of silly season match plays more into Phil’s hands than Tiger’s. Phil will be better at enjoying this moment and performing well than Tiger.”

“Phil has been in Tiger’s shadow his whole career. He’s going to do everything he can to declaw him. Plus, I’m not sure there is a better gambler on Tour than Phil. His $hit-talking game is going to be on point, and Tiger will be rattled… Phil, 2 up.”

“Phil is a seasoned gambler. Tiger is hyped about doing some serious gambling. This is just another Tuesday for Phil on the golf course.”

“I think it means more to Phil… just a hunch, but I think he will be ready.”

“Because this is a joke of a tournament.”

“Phil will win because Vegas will make Tiger let him, so they can do this match again. Then Tiger will win the second and third match. This will be a huge money maker for three years and then will fizzle out.”

“Phil is a seasoned gambler. Tiger is hyped about doing some serious gambling. This is just another Tuesday for Phil on the golf course.”

“Because everyone else is picking Tiger.”

“Phil is taking it way more seriously. Course recon and way more to gain will give Phil a massive edge. Tiger has nothing to gain from a win. Phil wins 2&1.”

“I picked Phil because I can’t pick both. I think it’s going to be a tie and they split the money.”

“I know Tiger is a big favorite and playing better as of late, but it’s hard to bet against Phil playing gambling desert golf in Vegas. Will they play ‘grease’ or ‘no grease.’”

“He’s a gambler and isn’t afraid to lose his entire fortune.”

“Tiger had his day at the Tour Championship. I think his form will decline from here!”

“Phil always plays for money. His side action game is better than his tournament game.”